Ketone alcohols.



UNITED STATES PATENT OFFICE.

GEORG- MEBLING AND HUGO KOHlLER, OF ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABRIKEN VORM. FBIEDB. BAYER 6c 60., OF ELBEBFELD, GERMANY, A

CORPORATION OF GERMANY.

KE'IONE .AlLCOHOLS.

No Drawing.

Application filed December 17,

To all whom it may concern:

Be it known that we, Gnono Mnnnnfo, professor of chemistry, doctor of philosophy, and HUGO Konnnn, doctor of philosophy,

chemist, citizens of the German Empire, re-

siding at.Elberfeld, Germany, have invented new and useful Improvements in Ketone condensing agents exercising a mild action Alcohols, of which the following is a specification. I

'Our invention relates to the manufacture.

and production of new valuable products being ketone'alcohols which products are obtained by treating acetone or its homologues,

- i such as ethyl-methyl-ketone with formal- 1.5

dehydeor compounds capable of generating formaldehyde inthe presence of alkaline on the components to be condensed. Such condensing agents are c. g. sodium or potassiu'm carbonate, magnesium carbonate or oxid, bisodium phosphate, borax, etc.

The new compounds are limpld oils soluble in ether, alcohol and benzene and possess the general formula I n -oo-tn-on -on in which;--R means an alkyl grou ,and R the group O H which group inc udes hyaeid anhydrid they are converted into the acetyl' compounds. I

In order to illustrate the new process more fully the following example is given,

the parts being by weight. A'mixture of three parts of acetone with one, part of a 35 per cent. formaldehyde is shaken together for some Hours with a concentrated aqueous solution of 0.02 to 0.06 parts of potassium carbonate until in a test portion diluted with water formaldehyde can no longer be detected. To carry out this test, some drops of an aqueous solution of acetate of anilin are added to the diluted liquid which is then allowed to stand for 15 minutes.- If after this time no precipitation or clouding due to the formation of methylene anilin is observed, the liquid is free from formaldehyde. The temperature of the liquid slowly rises Specification of Letters Patent.

1909. Serial No. 533,698. (Specimens) to 30-35 C. and it is kept at this acetyl compound Patented Apr. 18, 1911.

oint by cooling. The liquid is then placed into a separatory funnel and the lower layer containing the potash solution is removed. The thus obtained li uid is carefully neutralized with dilute hy rochloric or sulfuric acid, 1

the potassium chlorid or sulfate is filtered off and the filtrate is.distilled in cacao, the vessel being-heated on awater bath. Acetone and water pass over, while the new ketobutanol:

remains as a thick oil. The crude product boils at from 95 to 120 at 30 mm. ressure and upon completion of the distil ation a. higher boiling dark colored oil remains which on cooling changes into a tenacious syrup. After a second distillation the ketobutanol boils at 109-110 C. at 30 mm. res; sure. It is a limpid colorless oil solub e in water, alcohol and ether. On being kept for some time it changes into a tenacious syru insoluble in water. On being boiled wit acetic acid anhydrid it is converted into the a limpid, stable oil'boiling at 96 at 15-min;

pressure which does not change on. being he t. The formation of the product probab y takes place according to the following formula: CH,CO-CH +GH O= CH CO.CH. ,-CH,OH. The new methylketobutanol obtained in an analogous manner from ethylmethylketone and formaldehyde is a color ess oil boiling at 9095 C. at15 mm. pressure having probably the formula:

Other ketones may be used.

The compounds thus obtained are valuable intermediate products for the production of harmaceutical products or other valuable odles.

We claim:

1. The herein described ketone alcohols, obtainable by reacting upon ketones with formaldehyde having the general formula:

| v 1 f v R -COOH-OH,OH

in which-R means an alkyl group and R the group O H J, which products are limpid oils soluble in ether alcohol and benzene and convertible into acetates on bein boiled with acetic acid anhydrid, substantlally as described. I

2. The herein described ketobutanol, ob

'tainable by reacting upon acetone with for-' maldehyde, which is a limpid colorlessoil boiling at 109110 C. at 30 mm. "pressure soluble'in water, alcohol, ether-and benzol,, being converted into the acetyl compound on being boiled with acetic acid ,anhydrid,

which acetyl compound is a limpid oil boi1-' ing M969 0. at 15 mm. pressure, substantially as described.

In testimony whereof we have hereunto '25 set our hands in the presence of two sub-- scribing witnesses. J a

- GEORG'MERLING. [11. s.] I

HUGO K6HLER. [L. s'.]

Witnesses: v

O'rro Komc, CHAS. J. WRIGHT. 

